2 Financial Update 3 March 31, For the Years Ended, ($ in - PowerPoint PPT Presentation

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Financial Update 3

March 31, For the Years Ended, ($ in millions, except per share) 2019 2018 2017 2016 2015 2014 Income Statement Data: Gross Written Premiums $ 622 $ 1,821 $ 1,439 $ 1,269 $ 1,161 $ 1,137 Net Earned Premiums 312 1,262 1,035 890 847 874 Net Underwriting Income (Loss) 29 (39) (79) 53 127 205 Comprehensive Net Income (Loss) 76 (80) (78) (34) 196 186 Balance Sheet Data: Total Cash and Investments $ 3,593 $ 3,542 $ 3,604 $ 3,815 $ 3,678 $ 3,290 Total Assets 6,307 6,008 5,824 5,167 5,092 5,192 Debt 686 697 723 396 403 403 Total Liabilities 4,291 4,069 3,800 2,927 2,883 3,179 Series B preference shares 241 232 - - - - Common Equity 1,773 1,704 1,917 1,988 1,959 1,763 Total Liabilities & Equity $ 6,307 $ 6,008 $ 5,824 $ 5,167 $ 5,092 $ 5,192 Key Financial Indicators: GAAP Combined Ratio 91% 103% 108% 94% 85% 77% Cats impact on combined ratio 1% 15% 25% 12% 2% 7% Book Value Per Common Share $ 15.38 $ 14.80 $ 15.98 $ 16.57 $ 16.33 $ 14.69 Adjusted Book Value Per Share (1) $ 15.82 $ 15.24 $ 15.98 $ 16.57 $ 16.33 $ 14.69 (1) Adjusted book value per share is derived by dividing adjusted book value (common equity plus series B preference share amount reflected in mezzanine equity, and earned portion of future proceeds from stock option awards) by adjusted shares outstanding (common shares outstanding plus series B preference shares outstanding and earned portion of share-based compensation awards). See appendix for reconciliation of non-GAAP measures. 4

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Business Overview 8

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Executive Management Committee  Kip Oberting | Group President & CEO Monica Cramér-Manhem | Group COO, Gene Boxer | Chief Strategy Officer & Group Sirius Tenure: 15 | Relevant Experience: 23 Sirius International - President & CEO General Counsel Sirius Tenure: 33 | Relevant Experience: 33 Sirius Tenure: 3 | Relevant Experience: 20 Other Global Corporate Team Members   Ralph Salamone | Group CFO Jeff Davis | Group Chief Actuary & CRO Matthew Kirk | Investment Advisors President Sirius Tenure: 22 | Relevant Experience: 31 Sirius Tenure: 11 | Relevant Experience: 28 Sirius Tenure: 17 | Relevant Experience: 24 . Neal Wasserman | Global Solutions CEO Edward Park | Group Tax Director . Sirius Tenure: 19 | Relevant Experience: 33 Sirius Tenure: 3 | Relevant Experience: 21 12 .

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Gallatin Point Capital Bain Capital Credit Centerbridge Partners CM Bermuda, Ltd. The Carlyle Group Former Easterly investors Sirius International Insurance Group, Ltd. Other public shareholders Sirius Group Board of Directors Meyer (Sandy) Frucher Vice Chairman, Nasdaq Rachelle C. Keller Former Managing Director, Citibank James (Jim) B. Rogers, Jr International investor, author and commentator Alain Karaoglan Former COO, Voya Robert (Rob) L. Friedman Former CIO, the Mutual Series funds Kernan (Kip) Oberting CEO, Sirius Group Feng (Laurence) Liao CEO, CMIG International Various insurance and financial regulators around the globe, primarily: • Bermuda Monetary Authority • U.K. Prudential Regulation Authority • Swedish Financial Services Authority • N.Y. Department of Financial Services • Lloyds 14

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March 31, For the Years Ended, (in millions, except per share) 2019 2018 2017 2016 2015 2014 slide 4 - adjusted book value per share GAAP common equity $ 1,773 $ 1,704 $ 1,917 $ 1,988 $ 1,959 $ 1,763 Series B preference shares 241 232 - - - - Future proceeds from stock option awards 1 - - - - - Adjusted book value $ 2,014 $ 1,936 $ 1,917 $ 1,988 $ 1,959 $ 1,763 Common shares outstanding 115.262 115.151 120.000 120.000 120.000 120.000 Series B preference shares outstanding 11.902 11.902 Earned share-based compensation, excl stock options 0.095 - - - - - Stock option awards issued 0.038 - - - - - Adjusted shares outstanding 127.297 127.053 120.000 120.000 120.000 120.000 Book value per common share $ 15.38 $ 14.80 $ 15.98 $ 16.57 $ 16.33 $ 14.69 Adjusted book value per share $ 15.82 $ 15.24 $ 15.98 $ 16.57 $ 16.33 $ 14.69 26